3-{3-[2-(Propane-1-sulfonylamino)-ethyl]-5-pyridin-3-ylmethyl-phenyl}-propionic acid

ID: ALA113753

PubChem CID: 10834261

Max Phase: Preclinical

Molecular Formula: C20H26N2O4S

Molecular Weight: 390.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCS(=O)(=O)NCCc1cc(CCC(=O)O)cc(Cc2cccnc2)c1

Standard InChI:  InChI=1S/C20H26N2O4S/c1-2-10-27(25,26)22-9-7-17-11-16(5-6-20(23)24)12-19(13-17)14-18-4-3-8-21-15-18/h3-4,8,11-13,15,22H,2,5-7,9-10,14H2,1H3,(H,23,24)

Standard InChI Key:  NEWMAOXVMHXXRT-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 28  0  0  0  0  0  0  0  0999 V2000
    3.4792   -4.7292    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    3.4750   -5.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4792   -3.9042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7542   -4.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -8.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2000   -4.3167    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.6042   -4.8792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.4292   -8.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0250   -6.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3292   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7417   -5.6375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0542   -4.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4792   -4.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3125   -5.6042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7667   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7167   -7.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0042   -6.8542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0000   -8.5042    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.1875   -4.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9042   -4.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9042   -4.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6250   -4.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5917   -5.7000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1667   -5.6750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0542   -4.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8750   -6.0917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3375   -5.1375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  2  0
  4 12  1  0
  5 16  1  0
  6  1  1  0
  7 21  1  0
  8  5  2  0
  9 14  2  0
 10 22  1  0
 11  9  1  0
 12 10  2  0
 13  4  1  0
 14 10  1  0
 15  1  1  0
 16 17  1  0
 17  9  1  0
 18  5  1  0
 19 13  1  0
 20  6  1  0
 21 19  2  0
 22 20  1  0
 23 26  1  0
 24 19  1  0
 25 15  1  0
 26 24  2  0
 27 25  1  0
  4 11  2  0
 23  7  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA113753

   3-{3-[2-(Propane-1-sulfonylamino)-ethyl]-5-pyridin-3-ylmethyl-phenyl}-propionic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 390.51

Molecular Weight (Monoisotopic): 390.1613

AlogP: 2.56

#Rotatable Bonds: 11

Polar Surface Area: 96.36

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.06

CX Basic pKa: 5.43

CX LogP: 1.58

CX LogD: -0.17

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.61

Np Likeness Score: -0.78

References

1. Dickinson RP, Dack KN, Long CJ, Steele J..  (1997)  Thromboxane modulating agents. 3. 1H-imidazol-1-ylalkyl- and 3-pyridinylalkyl-substituted 3-[2-[(arylsulfonyl)amino]ethyl]benzenepropanoic acid derivatives as dual thromboxane synthase inhibitor/thromboxane receptor antagonists.,  40  (21): [PMID:9341919] [10.1021/jm9702793]

Source

Source(1):

• Scientific Literature